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A new synthesis of 1-deoxy-d-psicose and 1-deoxy-d-tagatose

✍ Scribed by Isidoro Izquierdo Cubero; Diego Garcia Poza

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 294 KB
Volume: 138
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)85231-9

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✦ Synopsis

As a part of our work on the use of enulose derivatives, obtained from aldehydo sugars either by the Knoevenagel-Doebner reaction' or by the Wittig reaction*, as starting products for the synthesis of hexulosesl, l-deoxyhexuloses1,3, and branched-chain deoxyhexuloses4, the title compounds were required. 1-Deoxy-D-tagatose5 and 1-deoxy-D-psicose 6,' have been synthesised by the diazoketone method and the L isomer of the latter compound has been reported8. We now describe a new synthesis route for the title compounds.

Hydroxylation of (Z)-1,3,4-trideoxy-5,6-O-isopropylidene-D-g~yce~o-hex-3enulose (1) with osmium tetraoxide gave 1-deoxy-5,6-O-isopropylidene-D-lyxohexulose (2) and 1-deoxy-5,6-0-isopropylidene-D-ribo-hexulose

(3), which were isolated by column chromatography.

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